Chicago

Chicago: The Windy City Awaits

Chicago, the third-largest city in the United States, sits on the southwestern shore of Lake Michigan and rewards visitors with a remarkable range of experiences. It is a city where bold architecture lines the riverfront, where deep-dish pizza is a matter of civic pride, and where distinct neighborhoods each carry their own character, history, and food culture. A few days here barely scratches the surface.

Must-Visit Attractions

Willis Tower (formerly Sears Tower) At 1,450 feet, Willis Tower dominated the skyline for decades. Ride the express elevator to the 103rd-floor Skydeck and step out onto the glass-floored Ledge boxes for an unobstructed view over the city, the lake, and on a clear day, parts of four surrounding states.

Millennium Park The Crown Fountain, the Jay Pritzker Pavilion, and the “Cloud Gate” sculpture, locally called “The Bean,” are the main draws, but the park also hosts free summer concerts, outdoor film screenings, and winter ice skating. Arrive early on weekday mornings to beat the crowds around the sculpture.

Art Institute of Chicago One of the finest art museums in the world. Allow at least three hours for the Impressionist and Post-Impressionist galleries, the Thorne Miniature Rooms, and the Modern Wing. Admission is free for Illinois residents on Thursday evenings. The museum store carries well-chosen prints and art books at reasonable prices.

Navy Pier Stretching 3,300 feet into Lake Michigan, the pier offers boat tours, a Ferris wheel, a Shakespeare theater, and several restaurants. It draws large crowds in summer but remains a useful starting point for lake architecture boat tours, which are among the best ways to understand Chicago’s skyline.

The Chicago Riverwalk Running along the south bank of the Chicago River through downtown, the Riverwalk connects kayak rental docks, outdoor bars, a small kayak fishing area, and several food vendors. Walking its length takes about 30 minutes and gives a ground-level view of the city’s celebrated bridges and skyscrapers.

The 606 Trail A 2.7-mile elevated trail converted from a former rail line, running through the Wicker Park, Bucktown, and Logan Square neighborhoods. Popular with cyclists and runners, it also offers views into the backyards and rooftops of classic Chicago two-flats and greystone buildings.

Architecture

Chicago is widely regarded as the birthplace of the modern skyscraper, and the city treats its architecture as a serious cultural asset.

  • Chicago Architecture Center: The best starting point for visitors interested in the built environment. The center runs river cruises, walking tours, and boat tours, and its ground-floor exhibition explains the evolution of the Chicago frame and the influence of the Chicago School.
  • Rookery Building: One of the oldest remaining skyscrapers in the city, with a light court interior redesigned by Frank Lloyd Wright in 1905. Free to enter the lobby during business hours.
  • Chicago Cultural Center: Originally the city’s central library, the building contains two of the largest Tiffany glass domes in the world. Admission is free.
  • Wrigley Building and Tribune Tower: Two of the most recognizable buildings along the Magnificent Mile, worth seeing from street level for their stonework and detail.

Places to Eat

Chicago has a deep food culture that goes well beyond its famous hot dogs and deep-dish pizza. The restaurant scene spans everything from decades-old neighborhood institutions to some of the most acclaimed kitchens in the country.

Chicago-Style Deep Dish Lou Malnati’s and Giordano’s are the two most consistently recommended chains for deep-dish. For a single-location experience, Pequod’s Pizza in Lincoln Park is known for its caramelized cheese crust. Deep-dish takes 45 minutes to bake, so order when you sit down.

Chicago-Style Hot Dogs Portillo’s serves the classic version: an all-beef frankfurter on a poppy seed bun with yellow mustard, relish, onion, tomatoes, a dill pickle spear, sport peppers, and celery salt. No ketchup. This combination is called “dragged through the garden” and locals take it seriously.

Italian Beef The Italian beef sandwich, thinly sliced seasoned beef on Italian bread dipped in the cooking juices, is a Chicago original. Al’s Beef has several locations and is among the most recognized names for this sandwich. Order it “wet” to have the whole roll dunked in the au jus.

Girl & the Goat Chef Stephanie Izard’s flagship restaurant in the West Loop focuses on wood-fired dishes and shared plates with Mediterranean and global influences. Reservations book out weeks in advance. The restaurant is part of a corridor of excellent dining along Randolph Street known informally as Restaurant Row.

Au Cheval A small diner-style spot in the West Loop known for its double cheeseburger. Waits can exceed two hours on weekends; arrive when they open or put your name in and explore the neighborhood while you wait.

Xoco Rick Bayless’s fast-casual counter in River North serves Mexican street food, including caldos, tortas, and churros made from scratch. Lower price point than his flagship Frontera Grill next door, with comparable quality on the dishes it shares.

Smoque BBQ A no-frills spot in the Irving Park neighborhood with consistently praised brisket, ribs, and pulled pork. Worth the trip off the tourist trail.

Where to Stay

The Langham Chicago Located in a former IBM building designed by Mies van der Rohe, the Langham occupies a landmark tower above the Chicago River. Rooms are spacious by city standards, and the Chuan Body + Soul spa is one of the better hotel spas in the city.

The Four Seasons Hotel Chicago On the upper floors of a Michigan Avenue tower, the hotel offers lake and city views from many rooms. Well-positioned for the Magnificent Mile and convenient to the Art Institute and Millennium Park.

The Chicago Athletic Association Hotel A converted 1893 athletic club in a landmark building facing Millennium Park. The hotel maintains many original architectural details including the grand staircase and the wood-paneled Game Room bar. The rooftop Cindy’s bar has one of the better views in the Loop.

Hampton Inn Majestic Chicago Theatre District A mid-range option in a restored 1910s building in the Loop, within walking distance of the theater district, the Art Institute, and Millennium Park. Good value for the location.

Airbnb and Short-Term Rentals Renting in neighborhoods like Logan Square, Wicker Park, or Ukrainian Village puts you close to local restaurants, coffee shops, and transit while giving a more residential feel than the hotel-heavy downtown core.

Neighborhoods Worth Exploring

Wicker Park and Bucktown Two adjacent neighborhoods on the Northwest Side with a concentration of independent restaurants, vintage shops, record stores, and bars. Milwaukee Avenue is the main commercial strip. The neighborhood has the feel of a city within the city.

Logan Square One of the most active dining and bar scenes in Chicago, centered on Logan and Milwaukee Boulevards. The area is walkable, has a strong independent coffee culture, and is well served by the Blue Line El train.

Pilsen A predominantly Mexican-American neighborhood on the Lower West Side with colorful murals, taquerias, the National Museum of Mexican Art (free admission), and a growing number of galleries. Easy to reach by the Pink Line El.

Hyde Park Home to the University of Chicago and the Museum of Science and Industry, one of the largest science museums in the Western Hemisphere. Hyde Park is also where the Obama Presidential Center is being built. The neighborhood has a strong independent bookstore scene anchored by Seminary Co-op.

Chinatown Compact but active, Chicago’s Chinatown is centered on Cermak Road and Wentworth Avenue. Good for dim sum on weekend mornings, bubble tea, bakeries, and grocery shopping. Reachable by the Red Line El.

Greektown and Little Italy Adjacent neighborhoods on the Near West Side close to the United Center. Both have clusters of restaurants on Halsted Street and Taylor Street respectively that have served their communities for generations.

Activities and Experiences

Architecture Boat Tour A 90-minute narrated tour along the Chicago River and lakefront, offered by the Chicago Architecture Center and several private operators. Seeing the city from the water with informed commentary is the single best introduction to Chicago’s built environment.

Lincoln Park Zoo Free admission, open year-round, with a compact layout that can be covered in a couple of hours. The adjoining Lincoln Park Conservatory is also free and worth a visit for the tropical plant collections.

Museum Campus Three major institutions sit together on the lakefront just south of downtown: the Field Museum (natural history, including SUE the T. rex), the Shedd Aquarium, and the Adler Planetarium. A combination ticket covers all three; plan a full day if you intend to see more than one seriously.

Wrigley Field Tour Even outside of game days, Wrigley Field offers guided tours of the 1914 ballpark, including the press box, dugouts, and the ivy-covered outfield walls. Cubs home games are a strong option in season; the neighborhood around the park, Wrigleyville, fills with fans for several hours before and after each game.

Chicago Blues and Jazz The city has a strong blues and jazz history. Andy’s Jazz Club in River North is a long-running venue with nightly live music and no cover charge at the bar. The Chicago Blues Festival in Grant Park runs each June and is free.

Chicago Cultural Center Events Free exhibitions, concerts, and lectures run throughout the year at the Cultural Center in the Loop. Check the city’s calendar before your visit; the programming is often high quality and completely free.

Getting Around

Chicago’s public transit network, operated by the CTA, covers most of the city effectively.

  • The El (elevated/subway trains): Eight color-coded lines connect the airports, downtown, and most neighborhoods. A Ventra card, loaded with transit value, is more economical than buying single-ride tickets. The Blue Line runs 24 hours and connects O’Hare Airport to downtown.
  • Buses: Cover areas the El does not reach. The CTA app and Google Maps both give accurate real-time arrival information.
  • Divvy Bikes: Chicago’s bike-share system has thousands of docks across the city. A day pass covers unlimited 30-minute rides. The Lakefront Trail, 18 miles of paved path along the lake, is one of the best cycling routes in any American city.
  • Ride-share: Uber and Lyft operate throughout the city and are practical for late-night travel or trips to neighborhoods not well served by the El.
  • Walking: The downtown Loop, Millennium Park, the Riverwalk, and the Magnificent Mile are all walkable from each other. Many visitors find they can cover central areas entirely on foot in good weather.

Practical Tips

  • Weather: Chicago earns its nickname. Wind off the lake makes temperatures feel significantly colder than the thermometer reads, particularly in fall and winter. Layers are useful even in summer, when lakefront evenings can be cool. Spring and fall are transitional and unpredictable; check the forecast daily.
  • Deep-dish timing: Order deep-dish as soon as you sit down. The 45-minute bake time is genuine, not a restaurant policy.
  • Museum passes: The Chicago CityPASS covers the Art Institute, Shedd Aquarium, Field Museum, Adler Planetarium, and either the Skydeck or the Museum of Science and Industry. Worth calculating against individual admissions if you plan to visit several.
  • Tap water: Chicago’s tap water is treated lake water and is safe to drink. Most locals drink it without filtering.
  • Tipping: Standard restaurant tipping practice applies: 18-20% at sit-down restaurants, $1-2 per drink at bars. Gratuity is sometimes added automatically for larger groups.
  • Neighborhoods after dark: The Loop and River North are active and well-lit at night. As in any large city, pay attention to your surroundings and avoid poorly lit areas in unfamiliar parts of the city after midnight.
  • Free days at museums: The Chicago Public Library system provides free museum passes that can be reserved online. Several museums, including the Art Institute, offer free admission on specific days or to specific groups.

Chicago rewards the visitor who ventures beyond the lakefront and downtown. The neighborhoods carry distinct histories and different versions of what the city is and has been. Allow time to get lost in them.